In the studies of Vietnamese territorial expansion, the perception of the ‘March to the South’ has become overwhelming in scholarship. Beginning in the 16th century and in collaboration with the group of Nguyễn Lords, the southward movement turned out to be most active and was able to reach the end of the long coast-line forming the shape of the letter S that characterizes modern Vietnam’s territory. Ever since then, the Việt people have been dominant in the Central region, the Lower Mekong and have even touched the Central Highlands in the West. Nevertheless, the Vietnamese history of going up to the mountains and going west started much earlier and it was another part of the history that has not been covered to any depth in Anglophone publications, despite a number of excellent works, especially in recent years (Anderson 2007, Churchman 2016, Baldanza 2016, Davis 2017, Anderson & Whitmore 2017, Lentz 2019, and others). While these authors so far have focused on the Sino-Vietnamese borderlands and the Northeast uplands, mostly over a limited period, this article offers an overview of the relationship between the Đại Việt central state and the entire upland regions through a ‘longue durée’ approach, from the Pre-Modern to the Early Modern periods. The Northwest region will be the focus both spatially and chronologically. Firstly, I seek to answer the following question: What were the conceptualizations that the Đại Việt imperial courts of Lý, Trần and Lê had built up towards the people and lands in the mountainous areas around Thăng Long (Hanoi), further up to the Northeast and especially the Northwest regions? Although retaining the traditional view of looking north from the delta, this study attempts to challenge the theoretical concept of ‘Zomia’ about the disjunction between highland and lowland polities, as seen from the case of Lý - Trần - Lê Đại Việt and its surrounding powers.